# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_124TCB_270K
_database_code_depnum_ccdc_archive 'CCDC 1028850'
_audit_update_record             
;
2015-02-23 deposited with the CCDC.
2015-03-27 downloaded from the CCDC.
;


# CHEMICAL DATA


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 1,2,4-trichlorobenzene 
;
_chemical_name_common            ?
_chemical_melting_point          290.07
_chemical_formula_moiety         'C6 H3 Cl3'
_chemical_formula_sum            'C6 H3 Cl3'
_chemical_formula_weight         181.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'


# CRYSTAL DATA


_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   3.8788(5)
_cell_length_b                   26.948(3)
_cell_length_c                   13.6006(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.164(9)
_cell_angle_gamma                90.00
_cell_volume                     1419.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    270.0(1)
_cell_measurement_reflns_used    4721
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      29.11

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    1.186
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_process_details   
;
Correction for absorption was made using CrysAlisPro,
Agilent Technologies, 2010.
;


_exptl_special_details           
;
Data were collected at ambient pressure (100 kPa) and 270.0(1) K with the
crystal obtained by the in-situ low-temperature crystallization
technique.
;


# EXPERIMENTAL DATA 


_diffrn_ambient_temperature      270.0(1)
_diffrn_ambient_pressure         100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur Eos'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 16.1544
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28754
_diffrn_reflns_av_R_equivalents  0.1340
_diffrn_reflns_av_sigmaI/netI    0.0503
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2503
_reflns_number_gt                1793
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2010)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2010)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (Macrae at al., 2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'


# REFINEMENT DATA 


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1338P)²+1.0016P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2503
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0756
_refine_ls_wR_factor_ref         0.2322
_refine_ls_wR_factor_gt          0.2070
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl11 Cl 0.7099(5) -0.03602(7) 0.13228(13) 0.0760(6) Uani 1 1 d . . .
Cl12 Cl 0.8447(5) -0.04918(6) 0.36170(13) 0.0750(6) Uani 1 1 d . . .
Cl14 Cl 0.3218(5) 0.13209(6) 0.41768(13) 0.0726(5) Uani 1 1 d . . .
C11 C 0.6073(14) 0.0100(2) 0.2132(4) 0.0510(13) Uani 1 1 d . . .
C12 C 0.6661(15) 0.0052(2) 0.3130(4) 0.0540(14) Uani 1 1 d . . .
C13 C 0.5818(14) 0.0428(2) 0.3756(4) 0.0532(14) Uani 1 1 d . . .
H13 H 0.6239 0.0393 0.4432 0.064 Uiso 1 1 calc R . .
C14 C 0.4350(15) 0.0856(2) 0.3375(4) 0.0528(13) Uani 1 1 d . . .
C15 C 0.3631(16) 0.0913(2) 0.2380(4) 0.0559(14) Uani 1 1 d . . .
H15 H 0.2592 0.1201 0.2130 0.067 Uiso 1 1 calc R . .
C16 C 0.4498(15) 0.0530(2) 0.1759(4) 0.0584(15) Uani 1 1 d . . .
H16 H 0.4022 0.0561 0.1084 0.070 Uiso 1 1 calc R . .
Cl21 Cl 0.7117(5) 0.21934(6) 0.17920(11) 0.0672(5) Uani 1 1 d . . .
Cl22 Cl 0.3442(4) 0.32223(6) 0.12286(10) 0.0656(5) Uani 1 1 d . . .
Cl24 Cl 0.3791(4) 0.37118(6) 0.50366(10) 0.0616(5) Uani 1 1 d . . .
C21 C 0.6188(14) 0.2624(2) 0.2688(4) 0.0495(13) Uani 1 1 d . . .
C22 C 0.4599(14) 0.3073(2) 0.2434(4) 0.0472(12) Uani 1 1 d . . .
C23 C 0.3914(14) 0.3417(2) 0.3155(4) 0.0473(12) Uani 1 1 d . . .
H23 H 0.2912 0.3722 0.2992 0.057 Uiso 1 1 calc R . .
C24 C 0.4771(13) 0.3292(2) 0.4131(4) 0.0454(12) Uani 1 1 d . . .
C25 C 0.6391(16) 0.2859(2) 0.4392(4) 0.0543(14) Uani 1 1 d . . .
H25 H 0.7024 0.2791 0.5048 0.065 Uiso 1 1 calc R . .
C26 C 0.7080(15) 0.2519(2) 0.3652(4) 0.0542(13) Uani 1 1 d . . .
H26 H 0.8154 0.2220 0.3816 0.065 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl11 0.0923(12) 0.0634(11) 0.0731(10) -0.0198(8) 0.0128(8) 0.0059(9)
Cl12 0.0907(13) 0.0506(9) 0.0835(11) 0.0143(8) 0.0036(9) 0.0145(8)
Cl14 0.0845(12) 0.0539(10) 0.0802(11) -0.0181(8) 0.0115(8) 0.0035(8)
C11 0.056(3) 0.045(3) 0.052(3) -0.005(2) 0.007(2) -0.007(2)
C12 0.057(3) 0.041(3) 0.065(3) 0.003(3) 0.011(3) -0.003(2)
C13 0.059(3) 0.050(3) 0.051(3) 0.006(3) 0.011(3) -0.001(3)
C14 0.054(3) 0.044(3) 0.061(3) -0.007(3) 0.010(2) -0.010(3)
C15 0.069(4) 0.037(3) 0.062(3) 0.008(2) 0.005(3) -0.003(3)
C16 0.063(4) 0.054(4) 0.059(3) 0.011(3) 0.009(3) -0.004(3)
Cl21 0.0829(11) 0.0557(9) 0.0645(9) -0.0157(7) 0.0166(8) 0.0015(7)
Cl22 0.0905(12) 0.0611(10) 0.0447(7) 0.0045(6) 0.0006(7) -0.0059(8)
Cl24 0.0823(11) 0.0535(9) 0.0505(8) -0.0091(6) 0.0159(7) -0.0017(7)
C21 0.047(3) 0.050(3) 0.051(3) -0.004(2) 0.005(2) -0.006(2)
C22 0.052(3) 0.050(3) 0.040(3) 0.005(2) 0.006(2) -0.008(2)
C23 0.056(3) 0.039(3) 0.047(3) 0.002(2) 0.009(2) -0.008(2)
C24 0.047(3) 0.044(3) 0.047(3) -0.003(2) 0.009(2) -0.009(2)
C25 0.068(4) 0.052(3) 0.042(3) 0.001(2) 0.000(2) -0.007(3)
C26 0.067(4) 0.040(3) 0.057(3) 0.006(2) 0.009(3) 0.002(3)


# MOLECULAR GEOMETRY


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl11 C11 1.720(6) . ?
Cl12 C12 1.736(6) . ?
Cl14 C14 1.733(6) . ?
C11 C12 1.369(8) . ?
C11 C16 1.393(8) . ?
C12 C13 1.375(8) . ?
C13 C14 1.374(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(8) . ?
C15 C16 1.386(8) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
Cl21 C21 1.734(6) . ?
Cl22 C22 1.723(5) . ?
Cl24 C24 1.730(5) . ?
C21 C26 1.367(7) . ?
C21 C22 1.394(8) . ?
C22 C23 1.386(8) . ?
C23 C24 1.392(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.363(8) . ?
C25 C26 1.398(8) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 C11 C16 119.1(5) . . ?
C12 C11 Cl11 122.3(5) . . ?
C16 C11 Cl11 118.6(4) . . ?
C11 C12 C13 120.7(5) . . ?
C11 C12 Cl12 120.0(5) . . ?
C13 C12 Cl12 119.3(4) . . ?
C14 C13 C12 119.6(5) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 121.5(5) . . ?
C13 C14 Cl14 119.0(4) . . ?
C15 C14 Cl14 119.5(5) . . ?
C14 C15 C16 118.2(5) . . ?
C14 C15 H15 120.9 . . ?
C16 C15 H15 120.9 . . ?
C15 C16 C11 120.9(5) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
C26 C21 C22 120.1(5) . . ?
C26 C21 Cl21 119.0(4) . . ?
C22 C21 Cl21 120.9(4) . . ?
C23 C22 C21 120.4(5) . . ?
C23 C22 Cl22 117.9(4) . . ?
C21 C22 Cl22 121.8(4) . . ?
C22 C23 C24 117.9(5) . . ?
C22 C23 H23 121.0 . . ?
C24 C23 H23 121.0 . . ?
C25 C24 C23 122.5(5) . . ?
C25 C24 Cl24 119.4(4) . . ?
C23 C24 Cl24 118.1(4) . . ?
C24 C25 C26 118.5(5) . . ?
C24 C25 H25 120.8 . . ?
C26 C25 H25 120.8 . . ?
C21 C26 C25 120.5(5) . . ?
C21 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 C11 C12 C13 -2.1(8) . . . . ?
Cl11 C11 C12 C13 179.8(4) . . . . ?
C16 C11 C12 Cl12 177.2(4) . . . . ?
Cl11 C11 C12 Cl12 -0.9(7) . . . . ?
C11 C12 C13 C14 0.4(9) . . . . ?
Cl12 C12 C13 C14 -178.9(4) . . . . ?
C12 C13 C14 C15 1.4(9) . . . . ?
C12 C13 C14 Cl14 178.6(4) . . . . ?
C13 C14 C15 C16 -1.4(9) . . . . ?
Cl14 C14 C15 C16 -178.6(4) . . . . ?
C14 C15 C16 C11 -0.4(9) . . . . ?
C12 C11 C16 C15 2.1(8) . . . . ?
Cl11 C11 C16 C15 -179.7(5) . . . . ?
C26 C21 C22 C23 0.0(8) . . . . ?
Cl21 C21 C22 C23 -179.1(4) . . . . ?
C26 C21 C22 Cl22 179.8(4) . . . . ?
Cl21 C21 C22 Cl22 0.6(7) . . . . ?
C21 C22 C23 C24 -1.8(8) . . . . ?
Cl22 C22 C23 C24 178.5(4) . . . . ?
C22 C23 C24 C25 3.2(8) . . . . ?
C22 C23 C24 Cl24 -177.9(4) . . . . ?
C23 C24 C25 C26 -2.8(8) . . . . ?
Cl24 C24 C25 C26 178.4(4) . . . . ?
C22 C21 C26 C25 0.4(8) . . . . ?
Cl21 C21 C26 C25 179.6(5) . . . . ?
C24 C25 C26 C21 0.9(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.773
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.113
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_124TCB_100K
_database_code_depnum_ccdc_archive 'CCDC 1028851'
_audit_update_record             
;
2015-02-23 deposited with the CCDC.
2015-03-27 downloaded from the CCDC.
;


# CHEMICAL DATA


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 1,2,4-trichlorobenzene 
;
_chemical_name_common            ?
_chemical_melting_point          290.07
_chemical_formula_moiety         'C6 H3 Cl3'
_chemical_formula_sum            'C6 H3 Cl3'
_chemical_formula_weight         181.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'


# CRYSTAL DATA


_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   3.7998(4)
_cell_length_b                   26.683(3)
_cell_length_c                   13.4964(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.665(9)
_cell_angle_gamma                90.00
_cell_volume                     1366.9(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    3761
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      29.03

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    1.232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_process_details   
;
Correction for absorption was made using CrysAlisPro,
Agilent Technologies, 2010.
;


_exptl_special_details           
;
Data were collected at ambient pressure (100 kPa) and 100.0(1) K with the
crystal obtained by the in-situ low-temperature crystallization
technique.
;


# EXPERIMENTAL DATA 


_diffrn_ambient_temperature      100.0(1)
_diffrn_ambient_pressure         100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur Eos'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 16.1544
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10317
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_sigmaI/netI    0.0466
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2419
_reflns_number_gt                2053
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2010)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2010)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (Macrae at al., 2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'


# REFINEMENT DATA 


_refine_special_details          
; 
 Refinement of F\^2\^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F\^2\^, conventional R-factors R are based 
 on F, with F set to zero for negative F\^2\^. The threshold expression of 
 F\^2\^ > 2sigma(F\^2\^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F\^2\^ are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;  
 calc w=1/[σ\^2\^(Fo\^2\^)+(0.0622P)\^2\^+0.6762P] where
 P=(Fo\^2\^+2Fc\^2\^)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2419
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1208
_refine_ls_wR_factor_gt          0.1125
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl11 Cl 0.7138(2) -0.03772(3) 0.13112(7) 0.0225(2) Uani 1 1 d . . .
Cl12 Cl 0.8519(2) -0.05092(3) 0.36283(7) 0.0217(2) Uani 1 1 d . . .
Cl14 Cl 0.3179(2) 0.13245(3) 0.42033(7) 0.0215(2) Uani 1 1 d . . .
C11 C 0.6026(9) 0.00889(13) 0.2125(3) 0.0156(7) Uani 1 1 d . . .
C12 C 0.6700(9) 0.00394(12) 0.3137(3) 0.0166(7) Uani 1 1 d . . .
C13 C 0.5855(8) 0.04194(12) 0.3776(3) 0.0155(7) Uani 1 1 d . . .
H13 H 0.6313 0.0385 0.4456 0.019 Uiso 1 1 calc R . .
C14 C 0.4316(9) 0.08520(12) 0.3393(3) 0.0150(7) Uani 1 1 d . . .
C15 C 0.3592(9) 0.09096(12) 0.2386(3) 0.0167(7) Uani 1 1 d . . .
H15 H 0.2540 0.1201 0.2138 0.020 Uiso 1 1 calc R . .
C16 C 0.4464(9) 0.05250(12) 0.1754(3) 0.0172(8) Uani 1 1 d . . .
H16 H 0.3999 0.0559 0.1075 0.021 Uiso 1 1 calc R . .
Cl21 Cl 0.7099(2) 0.21783(3) 0.17946(6) 0.0193(2) Uani 1 1 d . . .
Cl22 Cl 0.3323(2) 0.32154(3) 0.12198(6) 0.0189(2) Uani 1 1 d . . .
Cl24 Cl 0.3735(2) 0.37224(3) 0.50694(6) 0.0182(2) Uani 1 1 d . . .
C21 C 0.6174(9) 0.26195(12) 0.2693(2) 0.0145(7) Uani 1 1 d . . .
C22 C 0.4534(8) 0.30693(13) 0.2432(2) 0.0139(7) Uani 1 1 d . . .
C23 C 0.3817(8) 0.34169(12) 0.3169(3) 0.0146(7) Uani 1 1 d . . .
H23 H 0.2743 0.3721 0.3007 0.018 Uiso 1 1 calc R . .
C24 C 0.4739(9) 0.32987(12) 0.4146(2) 0.0139(7) Uani 1 1 d . . .
C25 C 0.6390(9) 0.28547(12) 0.4409(3) 0.0160(7) Uani 1 1 d . . .
H25 H 0.7001 0.2785 0.5070 0.019 Uiso 1 1 calc R . .
C26 C 0.7124(9) 0.25135(12) 0.3669(3) 0.0149(7) Uani 1 1 d . . .
H26 H 0.8256 0.2214 0.3832 0.018 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl11 0.0255(5) 0.0212(5) 0.0209(5) -0.0063(4) 0.0022(4) 0.0026(3)
Cl12 0.0245(5) 0.0167(4) 0.0238(5) 0.0046(3) -0.0004(4) 0.0038(3)
Cl14 0.0231(5) 0.0180(5) 0.0233(5) -0.0055(3) 0.0018(4) 0.0016(3)
C11 0.0158(17) 0.0160(17) 0.0153(18) -0.0041(14) 0.0034(14) -0.0011(13)
C12 0.0138(17) 0.0147(17) 0.0213(19) 0.0028(14) 0.0011(14) -0.0010(13)
C13 0.0127(17) 0.0187(18) 0.0149(18) 0.0028(14) -0.0008(14) -0.0018(13)
C14 0.0118(17) 0.0163(17) 0.0170(18) -0.0028(14) 0.0025(14) -0.0014(13)
C15 0.0150(18) 0.0136(17) 0.0217(19) 0.0015(14) 0.0020(15) -0.0010(13)
C16 0.0148(18) 0.0195(18) 0.0172(19) 0.0030(14) 0.0005(14) -0.0031(13)
Cl21 0.0215(5) 0.0181(4) 0.0185(5) -0.0051(3) 0.0035(4) 0.0005(3)
Cl22 0.0238(5) 0.0200(4) 0.0126(4) 0.0019(3) -0.0012(3) -0.0007(3)
Cl24 0.0234(5) 0.0170(4) 0.0144(5) -0.0027(3) 0.0033(4) -0.0002(3)
C21 0.0119(16) 0.0175(17) 0.0142(18) -0.0024(14) 0.0035(13) -0.0016(13)
C22 0.0127(17) 0.0171(17) 0.0122(18) 0.0024(14) 0.0025(13) -0.0034(13)
C23 0.0127(17) 0.0115(16) 0.0195(18) 0.0023(14) 0.0008(14) -0.0022(12)
C24 0.0139(17) 0.0150(17) 0.0132(17) -0.0046(14) 0.0047(13) -0.0038(13)
C25 0.0153(18) 0.0177(17) 0.0149(18) 0.0031(14) 0.0000(14) -0.0036(13)
C26 0.0155(17) 0.0110(16) 0.0184(18) 0.0036(14) 0.0023(14) 0.0008(13)


# MOLECULAR GEOMETRY


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl11 C11 1.725(3) . ?
Cl12 C12 1.737(3) . ?
Cl14 C14 1.737(3) . ?
C11 C12 1.383(5) . ?
C11 C16 1.389(5) . ?
C12 C13 1.379(5) . ?
C13 C14 1.383(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.382(5) . ?
C15 C16 1.384(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
Cl21 C21 1.737(3) . ?
Cl22 C22 1.724(3) . ?
Cl24 C24 1.738(3) . ?
C21 C26 1.379(5) . ?
C21 C22 1.390(5) . ?
C22 C23 1.396(5) . ?
C23 C24 1.385(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.379(5) . ?
C25 C26 1.389(5) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 C11 C16 119.5(3) . . ?
C12 C11 Cl11 121.3(3) . . ?
C16 C11 Cl11 119.2(3) . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 Cl12 118.7(3) . . ?
C11 C12 Cl12 120.6(3) . . ?
C12 C13 C14 119.1(3) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 121.5(3) . . ?
C15 C14 Cl14 119.6(3) . . ?
C13 C14 Cl14 118.9(3) . . ?
C14 C15 C16 118.7(3) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C15 C16 C11 120.6(3) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C26 C21 C22 120.9(3) . . ?
C26 C21 Cl21 118.4(3) . . ?
C22 C21 Cl21 120.7(3) . . ?
C21 C22 C23 119.6(3) . . ?
C21 C22 Cl22 122.2(3) . . ?
C23 C22 Cl22 118.3(3) . . ?
C24 C23 C22 118.5(3) . . ?
C24 C23 H23 120.7 . . ?
C22 C23 H23 120.7 . . ?
C25 C24 C23 122.2(3) . . ?
C25 C24 Cl24 119.1(3) . . ?
C23 C24 Cl24 118.7(3) . . ?
C24 C25 C26 118.8(3) . . ?
C24 C25 H25 120.6 . . ?
C26 C25 H25 120.6 . . ?
C21 C26 C25 120.0(3) . . ?
C21 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 C11 C12 C13 -0.4(5) . . . . ?
Cl11 C11 C12 C13 178.8(3) . . . . ?
C16 C11 C12 Cl12 177.9(3) . . . . ?
Cl11 C11 C12 Cl12 -2.9(4) . . . . ?
C11 C12 C13 C14 0.1(5) . . . . ?
Cl12 C12 C13 C14 -178.2(2) . . . . ?
C12 C13 C14 C15 0.4(5) . . . . ?
C12 C13 C14 Cl14 178.8(3) . . . . ?
C13 C14 C15 C16 -0.5(5) . . . . ?
Cl14 C14 C15 C16 -178.9(2) . . . . ?
C14 C15 C16 C11 0.2(5) . . . . ?
C12 C11 C16 C15 0.3(5) . . . . ?
Cl11 C11 C16 C15 -178.9(3) . . . . ?
C26 C21 C22 C23 -0.4(5) . . . . ?
Cl21 C21 C22 C23 179.9(2) . . . . ?
C26 C21 C22 Cl22 179.8(2) . . . . ?
Cl21 C21 C22 Cl22 0.1(4) . . . . ?
C21 C22 C23 C24 -0.7(5) . . . . ?
Cl22 C22 C23 C24 179.1(2) . . . . ?
C22 C23 C24 C25 1.2(5) . . . . ?
C22 C23 C24 Cl24 -178.1(2) . . . . ?
C23 C24 C25 C26 -0.5(5) . . . . ?
Cl24 C24 C25 C26 178.8(2) . . . . ?
C22 C21 C26 C25 1.1(5) . . . . ?
Cl21 C21 C26 C25 -179.3(3) . . . . ?
C24 C25 C26 C21 -0.6(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.117
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_124TCB_0.16GPa
_database_code_depnum_ccdc_archive 'CCDC 1028852'
_audit_update_record             
;
2015-02-23 deposited with the CCDC.
2015-03-27 downloaded from the CCDC.
;


# CHEMICAL DATA


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 1,2,4-trichlorobenzene 
;
_chemical_name_common            ?
_chemical_melting_point          290.07
_chemical_formula_moiety         'C6 H3 Cl3'
_chemical_formula_sum            'C6 H3 Cl3'
_chemical_formula_weight         181.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'


# CRYSTAL DATA


_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   3.8459(5)
_cell_length_b                   26.658(3)
_cell_length_c                   14.03(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.63(5)
_cell_angle_gamma                90.00
_cell_volume                     1436(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2687
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      29.53

_exptl_crystal_description       disc
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    1.173
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.39
_exptl_absorpt_correction_T_max  0.73
_exptl_absorpt_process_details   
; 
 Correction for absorption of the diamond-anvil cell and the sample 
 were made using program REDSHABS (Katrusiak, A. (2003) REDSHABS. Adam
 Mickiewicz University Poznań; Katrusiak, A. (2004) Z. Kristallogr.
 219, 461-467).
;


# EXPERIMENTAL DATA


_exptl_special_details           
;
Data were collected at room temperature and pressure of 0.16(5) GPa (160000
kPa) with the crystal obtained by the in-situ high-pressure
crystallization technique. Pressure was determined by monitoring the shift of
the ruby R1-fluorescence line.
;

_diffrn_ambient_temperature      295(2)
_diffrn_ambient_environment      'diamond-anvil cell'
_diffrn_ambient_pressure         160000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KUMA KM-4 CCD'
_diffrn_measurement_method       'φ- and ω-scans'
_diffrn_detector_area_resol_mean 8.1929
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7085
_diffrn_reflns_av_R_equivalents  0.1144
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         24.91
_reflns_number_total             540
_reflns_number_gt                404
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisCCD (Oxford Diffraction, 2009)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2010)'
_computing_data_reduction        
'CrysAlisPro (Agilent Technologies, 2010); REDSHABS (Katrusiak, A., 2003)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (Macrae at al., 2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'


# REFINEMENT DATA 


_refine_special_details          
; 
 Refinement of F\^2\^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F\^2\^, conventional R-factors R are based 
 on F, with F set to zero for negative F\^2\^. The threshold expression of 
 F\^2\^ > 2sigma(F\^2\^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F\^2\^ are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

 The diamond-anvil cell (DAC) imposes severe restrictions on which reflections
 can be collected, resulting in a low data:parameter ratio. 

 The distances between carbon atoms, within aromatic rings, were restrained to 
 be similar using the SADI instruction of SHELXL. The ISOR command (SHELXL) 
 was used to apply restraints on the Uij components of the chlorine atoms.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;  
 calc w=1/[σ\^2\^(Fo\^2\^)+(0.1157P)\^2\^+1.0915P] where
 P=(Fo\^2\^+2Fc\^2\^)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         540
_refine_ls_number_parameters     103
_refine_ls_number_restraints     56
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1895
_refine_ls_wR_factor_gt          0.1683
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl11 Cl 0.7088(8) -0.03591(11) 0.1306(10) 0.076(4) Uani 1 1 d U . .
Cl12 Cl 0.8421(7) -0.04901(9) 0.3613(10) 0.070(4) Uani 1 1 d U . .
Cl14 Cl 0.3207(7) 0.13213(9) 0.4179(9) 0.073(4) Uani 1 1 d U . .
C11 C 0.595(3) 0.0100(4) 0.215(2) 0.048(4) Uiso 1 1 d D . .
C12 C 0.664(3) 0.0057(3) 0.3102(19) 0.035(3) Uiso 1 1 d D . .
C13 C 0.585(2) 0.0426(3) 0.371(2) 0.055(3) Uiso 1 1 d D . .
H13 H 0.6320 0.0381 0.4362 0.066 Uiso 1 1 calc R . .
C14 C 0.439(3) 0.0858(3) 0.3388(18) 0.047(4) Uiso 1 1 d D . .
C15 C 0.368(3) 0.0912(4) 0.2441(18) 0.038(3) Uiso 1 1 d D . .
H15 H 0.2639 0.1204 0.2199 0.045 Uiso 1 1 calc R . .
C16 C 0.448(2) 0.0538(4) 0.184(2) 0.059(3) Uiso 1 1 d D . .
H16 H 0.4000 0.0582 0.1192 0.071 Uiso 1 1 calc R . .
Cl21 Cl 0.7123(7) 0.21942(9) 0.1793(8) 0.068(4) Uani 1 1 d U . .
Cl22 Cl 0.3459(9) 0.32228(11) 0.1234(10) 0.078(4) Uani 1 1 d U . .
Cl24 Cl 0.3769(7) 0.37119(9) 0.5034(9) 0.067(4) Uani 1 1 d U . .
C21 C 0.619(3) 0.2622(3) 0.261(3) 0.048(3) Uiso 1 1 d D . .
C22 C 0.461(3) 0.3075(4) 0.243(3) 0.049(3) Uiso 1 1 d D . .
C23 C 0.390(2) 0.3407(4) 0.314(2) 0.042(3) Uiso 1 1 d D . .
H23 H 0.2783 0.3708 0.2988 0.050 Uiso 1 1 calc R . .
C24 C 0.480(2) 0.3298(3) 0.408(2) 0.038(3) Uiso 1 1 d D . .
C25 C 0.635(2) 0.2853(3) 0.435(2) 0.055(3) Uiso 1 1 d D . .
H25 H 0.6903 0.2773 0.4988 0.065 Uiso 1 1 calc R . .
C26 C 0.705(3) 0.2532(4) 0.362(2) 0.037(3) Uiso 1 1 d D . .
H26 H 0.8163 0.2232 0.3789 0.044 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl11 0.0864(18) 0.0667(17) 0.076(13) -0.017(5) 0.002(5) 0.0045(13)
Cl12 0.0846(17) 0.0502(15) 0.076(13) 0.010(4) -0.002(5) 0.0116(11)
Cl14 0.0763(17) 0.0562(15) 0.087(12) -0.028(4) 0.010(4) 0.0027(11)
Cl21 0.0725(16) 0.0539(15) 0.078(12) -0.010(4) 0.007(4) 0.0006(10)
Cl22 0.0843(19) 0.0640(17) 0.084(13) 0.002(5) 0.004(5) -0.0096(14)
Cl24 0.0740(16) 0.0563(15) 0.070(12) 0.001(4) 0.004(4) -0.0010(11)


# MOLECULAR GEOMETRY


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl11 C11 1.78(2) . ?
Cl12 C12 1.745(16) . ?
Cl14 C14 1.74(2) . ?
C11 C12 1.347(16) . ?
C11 C16 1.354(17) . ?
C12 C13 1.350(15) . ?
C13 C14 1.346(13) . ?
C13 H13 0.9300 . ?
C14 C15 1.348(15) . ?
C15 C16 1.349(14) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
Cl21 C21 1.68(3) . ?
Cl22 C22 1.76(3) . ?
Cl24 C24 1.79(3) . ?
C21 C22 1.368(14) . ?
C21 C26 1.45(5) . ?
C22 C23 1.374(18) . ?
C23 C24 1.372(19) . ?
C23 H23 0.9300 . ?
C24 C25 1.371(13) . ?
C25 C26 1.372(19) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 C11 C16 116.3(17) . . ?
C12 C11 Cl11 123.9(10) . . ?
C16 C11 Cl11 119.7(19) . . ?
C11 C12 C13 121.5(15) . . ?
C11 C12 Cl12 121.8(11) . . ?
C13 C12 Cl12 116.6(15) . . ?
C14 C13 C12 121(2) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 118.3(17) . . ?
C13 C14 Cl14 121.0(18) . . ?
C15 C14 Cl14 120.6(8) . . ?
C14 C15 C16 119.6(15) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C11 123(2) . . ?
C15 C16 H16 118.5 . . ?
C11 C16 H16 118.5 . . ?
C22 C21 C26 113(3) . . ?
C22 C21 Cl21 126(3) . . ?
C26 C21 Cl21 120.7(9) . . ?
C21 C22 C23 123(3) . . ?
C21 C22 Cl22 117(3) . . ?
C23 C22 Cl22 120.1(12) . . ?
C24 C23 C22 120.7(15) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C25 C24 C23 121.7(17) . . ?
C25 C24 Cl24 116.2(19) . . ?
C23 C24 Cl24 121.9(8) . . ?
C24 C25 C26 116.0(19) . . ?
C24 C25 H25 122.0 . . ?
C26 C25 H25 122.0 . . ?
C25 C26 C21 125.4(13) . . ?
C25 C26 H26 117.3 . . ?
C21 C26 H26 117.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 C11 C12 C13 1.3(17) . . . . ?
Cl11 C11 C12 C13 177.2(7) . . . . ?
C16 C11 C12 Cl12 178.2(6) . . . . ?
Cl11 C11 C12 Cl12 -5.9(17) . . . . ?
C11 C12 C13 C14 -1.4(16) . . . . ?
Cl12 C12 C13 C14 -178.4(8) . . . . ?
C12 C13 C14 C15 1.2(15) . . . . ?
C12 C13 C14 Cl14 177.2(8) . . . . ?
C13 C14 C15 C16 -1.0(17) . . . . ?
Cl14 C14 C15 C16 -177.0(7) . . . . ?
C14 C15 C16 C11 1.0(16) . . . . ?
C12 C11 C16 C15 -1.1(16) . . . . ?
Cl11 C11 C16 C15 -177.2(9) . . . . ?
C26 C21 C22 C23 -0.7(18) . . . . ?
Cl21 C21 C22 C23 179.4(9) . . . . ?
C26 C21 C22 Cl22 180.0(10) . . . . ?
Cl21 C21 C22 Cl22 0.2(16) . . . . ?
C21 C22 C23 C24 1.2(17) . . . . ?
Cl22 C22 C23 C24 -179.6(10) . . . . ?
C22 C23 C24 C25 -2.0(16) . . . . ?
C22 C23 C24 Cl24 -177.7(7) . . . . ?
C23 C24 C25 C26 2.2(14) . . . . ?
Cl24 C24 C25 C26 178.2(7) . . . . ?
C24 C25 C26 C21 -1.8(16) . . . . ?
C22 C21 C26 C25 1.1(18) . . . . ?
Cl21 C21 C26 C25 -179.0(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.214
_diffrn_reflns_theta_full        24.91
_diffrn_measured_fraction_theta_full 0.214
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.053


_vrf_PLAT029_124TCB_0.16GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......       0.214 Note

RESPONSE: The Alerts generated below are the 'typical high-pressure
 crystallography warnings'. 
 1,2,4-Trichlorobenzene (124TCB) is a liquid at ambient conditions.
 A single crystal of 124TCB was obtained by the <i>in-situ</i>
 high-pressure crystallization technique in a diamond-anvil cell (DAC). 
 The DAC imposes severe restrictions on which reflections can be collected,
 resulting in incomplete data set and, as a result, in a low data:parameter
 ratio and low-bond precision. 
;


_vrf_PLAT201_124TCB_0.16GPa      
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......        12 Report

RESPONSE: All the carbon atoms, due to a low data:parameter ratio (see above),
 were refined with isotropic displacement parameters. 
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_124TCB_0.64GPa
_database_code_depnum_ccdc_archive 'CCDC 1028853'
_audit_update_record             
;
2015-02-23 deposited with the CCDC.
2015-03-27 downloaded from the CCDC.
;


# CHEMICAL DATA


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 1,2,4-trichlorobenzene 
;
_chemical_name_common            ?
_chemical_melting_point          290.07
_chemical_formula_moiety         'C6 H3 Cl3'
_chemical_formula_sum            'C6 H3 Cl3'
_chemical_formula_weight         181.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'


# CRYSTAL DATA


_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   3.7825(7)
_cell_length_b                   26.378(3)
_cell_length_c                   13.71(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.76(6)
_cell_angle_gamma                90.00
_cell_volume                     1365(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2420
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      29.34

_exptl_crystal_description       disc
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    1.234
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.38
_exptl_absorpt_correction_T_max  0.72
_exptl_absorpt_process_details   
; 
 Correction for absorption of the diamond-anvil cell and the sample 
 were made using program REDSHABS (Katrusiak, A. (2003) REDSHABS. Adam
 Mickiewicz University Poznań; Katrusiak, A. (2004) Z. Kristallogr.
 219, 461-467).
;


# EXPERIMENTAL DATA


_exptl_special_details           
;
Data were collected at room temperature and pressure of 0.64(5) GPa (640000
kPa) with the crystal obtained by the in-situ high-pressure
crystallization technique. Pressure was determined by monitoring the shift of
the ruby R1-fluorescence line.
;

_diffrn_ambient_temperature      295(2)
_diffrn_ambient_environment      'diamond-anvil cell'
_diffrn_ambient_pressure         640000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KUMA KM-4 CCD'
_diffrn_measurement_method       'φ- and ω-scans'
_diffrn_detector_area_resol_mean 8.1929
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6941
_diffrn_reflns_av_R_equivalents  0.1388
_diffrn_reflns_av_sigmaI/netI    0.0472
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         24.94
_reflns_number_total             528
_reflns_number_gt                434
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisCCD (Oxford Diffraction, 2009)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2010)'
_computing_data_reduction        
'CrysAlisPro (Agilent Technologies, 2010); REDSHABS (Katrusiak, A., 2003)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (Macrae at al., 2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'


# REFINEMENT DATA 


_refine_special_details          
; 
 Refinement of F\^2\^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F\^2\^, conventional R-factors R are based 
 on F, with F set to zero for negative F\^2\^. The threshold expression of 
 F\^2\^ > 2sigma(F\^2\^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F\^2\^ are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

 The diamond-anvil cell (DAC) imposes severe restrictions on which reflections
 can be collected, resulting in a low data:parameter ratio. 

 The distances between carbon atoms, within aromatic rings, were restrained to 
 be similar using the SADI instruction of SHELXL. The ISOR command (SHELXL) 
 was used to apply restraints on the Uij components of the chlorine atoms.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 calc w=1/[σ\^2\^(Fo\^2\^)+(0.1876P)\^2\^+0.0000P] where
 P=(Fo\^2\^+2Fc\^2\^)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         528
_refine_ls_number_parameters     103
_refine_ls_number_restraints     56
_refine_ls_R_factor_all          0.1279
_refine_ls_R_factor_gt           0.1112
_refine_ls_wR_factor_ref         0.3072
_refine_ls_wR_factor_gt          0.2840
_refine_ls_goodness_of_fit_ref   1.446
_refine_ls_restrained_S_all      1.423
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl11 Cl 0.7152(10) -0.03676(15) 0.1295(13) 0.064(5) Uani 1 1 d U . .
Cl12 Cl 0.8492(10) -0.05121(12) 0.3622(13) 0.061(5) Uani 1 1 d U . .
Cl14 Cl 0.3141(10) 0.13249(13) 0.4200(12) 0.061(4) Uani 1 1 d U . .
C11 C 0.588(3) 0.0091(4) 0.216(2) 0.022(3) Uiso 1 1 d D . .
C12 C 0.677(3) 0.0038(4) 0.314(2) 0.025(3) Uiso 1 1 d D . .
C13 C 0.583(3) 0.0418(4) 0.375(3) 0.043(4) Uiso 1 1 d D . .
H13 H 0.6179 0.0378 0.4425 0.051 Uiso 1 1 calc R . .
C14 C 0.439(3) 0.0858(4) 0.338(2) 0.030(4) Uiso 1 1 d D . .
C15 C 0.357(3) 0.0907(4) 0.240(2) 0.026(4) Uiso 1 1 d D . .
H15 H 0.2416 0.1196 0.2153 0.031 Uiso 1 1 calc R . .
C16 C 0.446(3) 0.0529(4) 0.178(3) 0.043(4) Uiso 1 1 d D . .
H16 H 0.4109 0.0570 0.1109 0.052 Uiso 1 1 calc R . .
Cl21 Cl 0.7143(10) 0.21743(14) 0.1816(12) 0.055(4) Uani 1 1 d U . .
Cl22 Cl 0.3344(10) 0.32139(14) 0.1243(12) 0.060(4) Uani 1 1 d U . .
Cl24 Cl 0.3664(10) 0.37251(12) 0.5075(13) 0.058(4) Uani 1 1 d U . .
C21 C 0.613(4) 0.2611(4) 0.274(4) 0.039(4) Uiso 1 1 d D . .
C22 C 0.457(3) 0.3063(5) 0.252(4) 0.036(4) Uiso 1 1 d D . .
C23 C 0.384(3) 0.3403(5) 0.322(3) 0.029(3) Uiso 1 1 d D . .
H23 H 0.2732 0.3708 0.3057 0.035 Uiso 1 1 calc R . .
C24 C 0.476(3) 0.3291(4) 0.417(3) 0.039(4) Uiso 1 1 d D . .
C25 C 0.632(3) 0.2851(4) 0.448(4) 0.044(4) Uiso 1 1 d D . .
H25 H 0.6813 0.2781 0.5139 0.053 Uiso 1 1 calc R . .
C26 C 0.712(3) 0.2518(5) 0.377(3) 0.036(4) Uiso 1 1 d D . .
H26 H 0.8324 0.2221 0.3950 0.043 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl11 0.074(2) 0.050(2) 0.069(13) -0.002(6) 0.007(6) 0.0037(17)
Cl12 0.076(2) 0.038(2) 0.069(13) 0.017(5) 0.001(5) 0.0108(14)
Cl14 0.071(2) 0.038(2) 0.075(13) -0.012(5) 0.011(5) 0.0034(14)
Cl21 0.064(2) 0.041(2) 0.064(13) -0.009(5) 0.030(5) 0.0001(14)
Cl22 0.071(2) 0.044(2) 0.065(13) 0.006(6) 0.012(6) -0.0046(16)
Cl24 0.067(2) 0.044(2) 0.064(13) -0.012(6) 0.015(5) -0.0014(14)


# MOLECULAR GEOMETRY


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl11 C11 1.78(3) . ?
Cl12 C12 1.71(2) . ?
Cl14 C14 1.75(3) . ?
C11 C16 1.36(2) . ?
C11 C12 1.367(19) . ?
C12 C13 1.370(19) . ?
C13 C14 1.367(17) . ?
C13 H13 0.9300 . ?
C14 C15 1.365(19) . ?
C15 C16 1.363(18) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
Cl21 C21 1.77(5) . ?
Cl22 C22 1.83(5) . ?
Cl24 C24 1.76(3) . ?
C21 C22 1.355(16) . ?
C21 C26 1.46(7) . ?
C22 C23 1.355(17) . ?
C23 C24 1.354(17) . ?
C23 H23 0.9300 . ?
C24 C25 1.357(16) . ?
C25 C26 1.355(17) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 C11 C12 122(2) . . ?
C16 C11 Cl11 116(2) . . ?
C12 C11 Cl11 121.6(11) . . ?
C11 C12 C13 117.9(18) . . ?
C11 C12 Cl12 122.0(13) . . ?
C13 C12 Cl12 119.6(18) . . ?
C14 C13 C12 120(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 121(2) . . ?
C15 C14 Cl14 120.8(10) . . ?
C13 C14 Cl14 118(2) . . ?
C16 C15 C14 119.4(18) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C11 119(3) . . ?
C15 C16 H16 120.3 . . ?
C11 C16 H16 120.3 . . ?
C22 C21 C26 116(4) . . ?
C22 C21 Cl21 122(4) . . ?
C26 C21 Cl21 121.9(11) . . ?
C21 C22 C23 122(4) . . ?
C21 C22 Cl22 119(4) . . ?
C23 C22 Cl22 119.2(12) . . ?
C24 C23 C22 119.1(17) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C23 C24 C25 124(2) . . ?
C23 C24 Cl24 118.5(11) . . ?
C25 C24 Cl24 117(2) . . ?
C26 C25 C24 116(2) . . ?
C26 C25 H25 121.8 . . ?
C24 C25 H25 121.8 . . ?
C25 C26 C21 121.9(17) . . ?
C25 C26 H26 119.1 . . ?
C21 C26 H26 119.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 C11 C12 C13 7.3(17) . . . . ?
Cl11 C11 C12 C13 177.1(9) . . . . ?
C16 C11 C12 Cl12 179.1(10) . . . . ?
Cl11 C11 C12 Cl12 -11.1(16) . . . . ?
C11 C12 C13 C14 -6.7(16) . . . . ?
Cl12 C12 C13 C14 -178.8(9) . . . . ?
C12 C13 C14 C15 5.8(17) . . . . ?
C12 C13 C14 Cl14 178.5(9) . . . . ?
C13 C14 C15 C16 -5.2(19) . . . . ?
Cl14 C14 C15 C16 -177.7(9) . . . . ?
C14 C15 C16 C11 5.6(18) . . . . ?
C12 C11 C16 C15 -6.8(16) . . . . ?
Cl11 C11 C16 C15 -177.1(9) . . . . ?
C26 C21 C22 C23 -2(2) . . . . ?
Cl21 C21 C22 C23 -178.8(10) . . . . ?
C26 C21 C22 Cl22 178.7(13) . . . . ?
Cl21 C21 C22 Cl22 2.2(19) . . . . ?
C21 C22 C23 C24 1(2) . . . . ?
Cl22 C22 C23 C24 -179.8(12) . . . . ?
C22 C23 C24 C25 -2(2) . . . . ?
C22 C23 C24 Cl24 -177.8(9) . . . . ?
C23 C24 C25 C26 3.0(19) . . . . ?
Cl24 C24 C25 C26 179.3(10) . . . . ?
C24 C25 C26 C21 -4.2(18) . . . . ?
C22 C21 C26 C25 4(2) . . . . ?
Cl21 C21 C26 C25 -179.6(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.219
_diffrn_reflns_theta_full        24.94
_diffrn_measured_fraction_theta_full 0.219
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.128


_vrf_PLAT029_124TCB_0.64GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......       0.219 Note

RESPONSE: The Alerts generated below are the 'typical high-pressure
 crystallography warnings'. 
 1,2,4-Trichlorobenzene (124TCB) is a liquid at ambient conditions.
 A single crystal of 124TCB was obtained by the <i>in-situ</i>
 high-pressure crystallization technique in a diamond-anvil cell (DAC). 
 The DAC imposes severe restrictions on which reflections can be collected,
 resulting in incomplete data set and, as a result, in a low data:parameter
 ratio and low-bond precision. 
;

_vrf_PLAT201_124TCB_0.64GPa      
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......        12 Report

RESPONSE: All the carbon atoms, due to a low data:parameter ratio (see above),
 were refined with isotropic displacement parameters. 
;

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